For most of Caleb’s life, it’s always been him and his little brother. 

After the passing of their parents (their father to a fever, and their mother to a witch trial), Caleb sought refuge and stability in the nearby town of Gravesfield, Connecticut. Years passed, and the two brothers succeeded in making lives for themselves as young witch hunters. Sure, the work wasn’t exactly... savory to commit, in Caleb’s opinion, but it was their best chance at belonging to this town. It was their best chance at having a home.

Everything changed though when Caleb met Evelyn. He hadn’t expected to stumble across everything that he did when he met her. He hadn’t expected to learn that she was a witch, of all things, but... well, she was was far from the monstrous or wicked depiction that the people of his town had described witches to be. In the end, she was actually quite kind to him, and she told him tales of her home, a land where the ocean boils and the skies are purple. He remained in contact with her, and through Evelyn, Caleb became the first human to set foot on the Boiling Isles. The land was just as horrifying as it was amazing, and the magic and life settled atop it was purely a sight to behold. Caleb fell in love with all of it ...and in time, he fell in love with Evelyn too.

Despite Caleb’s revelations, the witch trials in Gravesfield continued, and watching the countless executions took too much of a toll. What would happen to him if his town knew he was cavorting with a witch? What would happen to Evelyn...?

Eventually, a fire broke out. The town was in a frenzy, and in the madness of it all, Caleb Wittebane was spirited away by a witch, never to look back... He arrived on the Boiling Isles, and this time, it was for good. For a long time, it was really good. The life that Caleb had chosen to build with Evelyn was a beautiful one, and with Flapjack at his side, and his first child on the way, Caleb could say that he was happy

...and then Philip entered his life again. His brother had crossed dimensions to find him, and at first, Caleb was overjoyed to see him once again. They could live in this world together, make a home for themselves that was finally safe, and warm, and happy. That didn’t happen. Instead, Caleb discovered his brother’s curse, horrified at what he had done to himself. Worst was Philip’s reaction to the news that Caleb would be having a child with Evelyn. There was no happiness to be found, only anger and sorrow all around. 

It was only anger that Caleb saw when he died, a knife in his chest, and his brother standing as the culprit.